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9 Creative Ways To Style Shorts

Shorts are inherently comfortable. That's a huge part of their appeal. But when it comes to styling shorts, a lot of guys aren't so comfortable choosing the right shorts or what to wear with them.
Most guys don't wear shorts quite as often as they do long pants. That may be a contributing factor to any hesitation when it comes to rocking shorts or showing your legs (if your legs are pale, that'll go away after a few times wearing shorts).
But you don't have to be a tanned lifeguard or tennis instructor to feel comfortable and look like you belong in shorts. It's actually not much different than styling pants, though there are a few tips that can help.
This guide covers when it's appropriate to wear shorts, tips for choosing shorts that will work for you, outfit examples for styling shorts for any occasion, and the four pairs of shorts you want in your closet.

When Are Shorts Appropriate, and When Are They Not?

Part of being confident wearing shorts is knowing that you're wearing them for the right occasion. You could wear great shorts with a carefully put-together outfit, but if it's in the wrong context it'll be a miss.
Fortunately, it's not that difficult to decipher when shorts are and aren't in your best interest.
If it's warm out, shorts are appropriate.
Unless you're heading to a more formal setting, such as work, a wedding, baptism, bar mitzvah, etc.
It's really as simple as that. If it's warm out, shorts are fair game unless you're heading to a formal event or somewhere there is a dress code that doesn't include shorts, like a nightclub or posh restaurant.
And then, of course, you might also want to avoid shorts in the cold weather. That should be pretty obvious; you'll be cold and may get some strange looks. But there are exceptions that allow wearing shorts in cold weather as well.
If you're exercising or playing a sport, shorts may be appropriate even if it's cold out.

How To Choose Shorts That Will Work for You

This section is really more about what to avoid when choosing shorts. There are four specific recommendations for shorts you need in your closet towards the end of this article.
In summary, before getting to what to avoid at all costs, you want to stick to shorts that are made from a comfortable material, fall above the knee, and are minimalistic in design.

What Shorts To Avoid

Avoid cargo shorts. Anything with protruding pockets that extend past your knees is out. Anything with dangling straps or a loop to hang a hammer is out.
Consider avoiding cargo shorts. If you need more convincing, here is a whole article on it.
Avoid shorts with pleats. We aren't even sure if these are made anymore (hopefully not), but if you shop at thrift stores you're sure to find them there. Don't wear pleated shorts; they're outdated and look puffy.
Avoid mesh shorts. Unless you're heading to PE or basketball practice, there's no real reason you need to be wearing mesh shorts.

Outfit Examples: Styling Shorts for Any Occasion

Shorts for Exercise

Shorts + Polo: Change up your exercise look by wearing shorts and polo instead of your usual t-shirt or cutoff. Polo shirts actually began in athletics, and have been a classy shirt to exercise in ever since.
Today you can get a polo made from stretchy, lightweight performance fabric with antimicrobial properties. This means you'll look fresh, feel fresh, and smell fresh regardless of your workout routine.
Polo shirts are also aesthetically complimentary to your physique. They emphasize the muscles in your chest and arms. Why not wear it with a pair of shorts for exercise in a classic, tennis-inspired look?
Shorts + Leggings: Guys can wear leggings too, especially under a pair of shorts. Just turn on an NBA game and see how many players are wearing them. Shorts with leggings is a trendy look with potential health and performance benefits as well.
You can find them in full length or three-quarters length. Neutral color leggings are a safe bet because they go with whatever shorts you choose.
Coordinate the color of your shorts to match your leggings, and wear a contrasting top. Alternatively, you can match the color of your leggings with your shirt, and show contrast with your shorts.
Earth Toned Outfit: So many workout clothes consist of neutral shades or bold colors like red, blue, and for some lousy reason... neon. Try something different by putting together an exercise outfit with only earth tonesThese super-light shorts come in dark olive as well as sand. This heather oat-colored performance tee will compliment it well.
Together they make an outfit that will look good anywhere and perform well in the gym. It will also stand out in a subtle way; an outfit that's head-to-toe performance fabric, yet with tasteful earth tones.

Cool and Casual

Shorts With Matching Sweatshirt: You can wear shorts with a matching sweatshirt the same way you'd match joggers and a sweatshirt. It's a comfortable and sporty outfit that looks put together for a casual vibe.
Sticking a basic shorts and sweatshirt combination will make a solid blank canvas to show your personal style through details. Wear sneakers with a bit more flair, tasteful jewelry, or a crossbody bag to polish off the look.
Shorts + Belt + Unbuttoned Shirt: Wearing shorts with an unbuttoned shirt is a laid-back look that benefits from the traditional factor of a button-up shirt. You can pull off this look with either a long sleeve or a short-sleeve button-up.
Choose shorts with belt loops to rock a belt with this look. It adds structure to your outfit while keeping the overall look relaxed. Sneakers, boat shoes, or loafers will look natural with this easygoing outfit.
Solid Shorts and Shirt + Trendy Socks: The goal of this look is to coordinate your shorts and shirt and allow your socks to take the spotlight. Socks don't usually get a chance to be the main attraction. They're usually either hidden away under pants or are worn out of necessity, as plain essentials free from color or pattern.
Even just some classic retro stripes around your ankles can set off an outfit. You can of course wear a wilder pattern if you're so inclined.
In order to make it work, select shorts and a shirt that is either the same color or the same shade. Pick out your socks so that they are a complimentary color to your outfit.
For example, wear navy shorts, a light blue shirt, and white ringers socks with orange or yellow stripes.

Look Sharp in Shorts

Shorts + Short Sleeve Button Up: A short-sleeve button-up is a logical choice to wear with shorts. If you're going for a more dressed-up look, you'll want to wear it tucked in with a belt. Of course, match your belt with your shoes.
It's common to find short-sleeve button-ups in all sorts of wild prints and patterns. These are fine but tend to look more casual. Opt for a solid color shirt in a light shade in order to achieve a look that will be sharp in the office or an important meeting.
Shorts + Polo + Sweater: This outfit is a classic preppy look. Shorts and a polo is a sporty combination that is elevated by adding a sweater. Wear it over the shirt and let the collar pop out from underneath.
Complete this outfit with socks that follow the color scheme and minimalistic leather sneakers, loafers, or oxfords.
Shorts + Blazer: Here's a look that's proven to be fashionable in recent years by figures like LeBron James, ASAP Rocky, and Pharrell Williams. But you don't have to be a celebrity or attend a red carpet event to pull it off.
Play down the look by selecting an unstructured blazer, and opting out of the tie. Instead, wear a v-neck or solid t-shirt. Match the blazer to your shorts, or choose colors that you would if you were wearing long pants, like grey or khaki shorts with a navy blazer.

4 Shorts You Need for Your Wardrobe

Shorts fulfill a few different needs in your wardrobe. You need shorts to work out in, shorts to swim in, shorts for hot weather, and shorts for lounging. Some shorts can cover more than one of these needs. The following four shorts are all you need to achieve the looks mentioned above.

All Day Every Day Short


Flex Short


Workday Short


Weekend Short


Look Forward To Shorts Weather

Shorts are just like any other piece of clothing in that they can be flattering or unflattering depending on the design, how they fit, and what you wear them with. After reading through this guide, you should have an idea as to the shorts you're looking for and the many ways you can style them for any occasion.
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